Aspects of the present invention relate in general to computer system management and in particular to a method and a system of managing failures in software deployments. One common type of software deployment is an operating system deployment. An operating system deployment is the process whereby an operating system is installed on a computing machine. The machine to which an operating system is being deployed is often referred to as the target machine. The process of deploying an operating system to a target machine involves a number of management tasks that are performed in a specific order until the software installation is completed. However, in the process of deploying the operating system, errors or failures may occur. Errors that occur during the execution of a given task may impact the execution of other tasks. Managing failures or errors during an operating system deployment to a target machine is can be problematic as the target machine has limited capabilities until the deployment of the operating system is complete.